Classification Term: 1470

Cucurbitacins (ontology term: CHEMONTID:0001686)

Polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions." [ASIN:B004GEAWLS]

found 20 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Steroids and steroid derivatives

Child Taxonomies: There is no child term of current ontology term.

Cucurbitacin B

(R,E)-6-((2S,8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate

C32H46O8 (558.3192516)


Together wth other cucurbitacins, is responsible for the bitter taste and toxic props. of spoilt cucumbers. Cucurbitacin B is found in many foods, some of which are muskmelon, bitter gourd, green vegetables, and cucumber. Cucurbitacin B is found in bitter gourd. Together wth other cucurbitacins, is responsible for the bitter taste and toxic properties of spoilt cucumber Cucurbitacin B is a cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 5 and 23; a hydroxy function at C-25 is acetylated. It is a cucurbitacin, a secondary alpha-hydroxy ketone and a tertiary alpha-hydroxy ketone. It derives from a hydride of a lanostane. Cucurbitacin B is a natural product found in Begonia plebeja, Trichosanthes miyagii, and other organisms with data available. Cucurbitacin B belongs to a class of highly oxidized tetracyclic triterpenoids and is oral active. Cucurbitacin B inhibits tumor cell growth, migration and invasion and cycle arrest, but induces cell apoptosis. Cucurbitacin B has potent anti-inflammatory, antioxidant, antiviral, hypoglycemic, hepatoprotective, neuroprotective activity[1][2][3][4][5]. Cucurbitacin B belongs to a class of highly oxidized tetracyclic triterpenoids and is oral active. Cucurbitacin B inhibits tumor cell growth, migration and invasion and cycle arrest, but induces cell apoptosis. Cucurbitacin B has potent anti-inflammatory, antioxidant, antiviral, hypoglycemic, hepatoprotective, neuroprotective activity[1][2][3][4][5]. (+)-Cucurbitacin B. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=6199-67-3 (retrieved 2024-08-12) (CAS RN: 6199-67-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

Cucurbitacin D

17-[(E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione

C30H44O7 (516.3086874)


Cucurbitacin D is a cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 5 and 23. It is a cucurbitacin, a secondary alpha-hydroxy ketone and a tertiary alpha-hydroxy ketone. It derives from a hydride of a lanostane. Cucurbitacin D is a natural product found in Elaeocarpus chinensis, Elaeocarpus hainanensis, and other organisms with data available. Cucurbitacin D is found in calabash. Cucurbitacin D is isolated from plants of the Cucurbitacea Cucurbitacin D is an active component in Trichosanthes kirilowii, disrupts interactions between Hsp90 and two co-chaperones, Cdc37 and p23. Cucurbitacin D prevents Hsp90 client (Her2, Raf, Cdk6, pAkt) maturation without induction of the heat shock response. Anti-cancer activity[1]. Cucurbitacin D is an active component in Trichosanthes kirilowii, disrupts interactions between Hsp90 and two co-chaperones, Cdc37 and p23. Cucurbitacin D prevents Hsp90 client (Her2, Raf, Cdk6, pAkt) maturation without induction of the heat shock response. Anti-cancer activity[1].

   

Cucurbitacin C

(3E)-6-[5,13-Dihydroxy-1-(hydroxymethyl)-6,6,11,15-tetramethyl-17-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetic acid

C32H48O8 (560.3349008)


Cucurbitacin C is found in cucumber. Cucurbitacin C is a constituent of Cucurbitaceae, e.g. Cucumis sativus (cucumber) Constituent of Cucurbitaceae, e.g. Cucumis sativus (cucumber). Cucurbitacin C is found in cucumber and fruits.

   

3beta-Cucurbita-5,24-dien-3-ol

(3S,9R,13R,14S)-4,4,9,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol

C30H50O (426.386145)


3beta-Cucurbita-5,24-dien-3-ol is found in bitter gourd. 3beta-Cucurbita-5,24-dien-3-ol is a constituent of pumpkin seeds. Constituent of pumpkin seeds. 3beta-Cucurbita-5,24-dien-3-ol is found in bitter gourd and green vegetables.

   

3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al

5,9-dihydroxy-14-[(4E)-6-methoxy-6-methylhept-4-en-2-yl]-6,6,11,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-1-carbaldehyde

C31H50O4 (486.37089000000003)


3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al is found in fruits. 3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al is a constituent of Momordica charantia (bitter melon). Constituent of Momordica charantia (bitter melon). 3,7-Dihydroxy-25-methoxycucurbita-5,23-dien-19-al is found in fruits.

   

(3b,7b,22x)-Cucurbita-5,24-diene-3,7,23-triol 7-glucoside

2-{[5-hydroxy-14-(4-hydroxy-6-methylhept-5-en-2-yl)-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C36H60O8 (620.428796)


(3b,7b,22x)-Cucurbita-5,24-diene-3,7,23-triol 7-glucoside is found in fruits. (3b,7b,22x)-Cucurbita-5,24-diene-3,7,23-triol 7-glucoside is a constituent of Momordica charantia (bitter melon). Constituent of Momordica charantia (bitter melon). (3b,7b,22x)-Cucurbita-5,24-diene-3,7,23-triol 7-glucoside is found in fruits.

   

Momordicoside L

3-hydroxy-17-[(E)-6-hydroxy-6-methylhept-4-en-2-yl]-4,4,13,14-tetramethyl-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-9-carbaldehyde

C36H58O9 (634.4080618)


Momordicoside L is found in bitter gourd. Momordicoside L is a constituent of Momordica charantia (bitter melon) Constituent of Momordica charantia (bitter melon). Momordicoside L is found in bitter gourd and fruits.

   

22-Deoxocucurbitacin D

14-[(4E)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-4,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,17-dione

C30H46O6 (502.3294216)


22-Deoxocucurbitacin D is found in green vegetables. 22-Deoxocucurbitacin D is a constituent of Lagenaria siceraria (bottle gourd) Constituent of Lagenaria siceraria (bottle gourd). 22-Deoxocucurbitacin D is found in green vegetables.

   

22-Deoxoisocucurbitacin D

14-[(4E)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-5,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-4,17-dione

C30H46O6 (502.3294216)


22-Deoxoisocucurbitacin D is found in green vegetables. 22-Deoxoisocucurbitacin D is a constituent of Lagenaria siceraria (bottle gourd) Constituent of Lagenaria siceraria (bottle gourd). 22-Deoxoisocucurbitacin D is found in green vegetables.

   

Cucurbitacin IIa

6-Hydroxy-2-methyl-5-oxo-6-{4,5,13-trihydroxy-1,6,6,11,15-pentamethyl-17-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}heptan-2-yl acetic acid

C32H50O8 (562.35055)


   

5alpha-Cucurbitane

4,4,9,13,14-pentamethyl-17-(6-methylheptan-2-yl)-2,3,5,6,7,8,10,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene

C30H54 (414.4225284)


   

Cucurbitacin B 2-sulfate

{14-[6-(acetyloxy)-2-hydroxy-6-methyl-3-oxohept-4-en-2-yl]-13-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-4-yl}oxidanesulphonic acid

C32H46O11S (638.2760686)


   

Cucurbitacin E

6-{4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-dien-14-yl}-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetic acid

C32H44O8 (556.3036024)


   

Cucurbitacin I

14-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-4,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-diene-5,17-dione

C30H42O7 (514.2930382)


   

Mogrol

17-(5,6-dihydroxy-6-methylheptan-2-yl)-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11-diol

C30H52O4 (476.3865392)


   

5beta,19-Epoxy-19-methoxycucurbita-6,23(E)-diene-3beta,25-diol

(1R,4S,5S,8R,9R,13S,16S,19R)-8-[(2R,4E)-6-hydroxy-6-methylhept-4-en-2-yl]-19-methoxy-5,9,17,17-tetramethyl-18-oxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-2-en-16-ol

C31H50O4 (486.37089000000003)


5beta,19-epoxy-19-methoxycucurbita-6,23(e)-diene-3beta,25-diol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 5beta,19-epoxy-19-methoxycucurbita-6,23(e)-diene-3beta,25-diol can be found in bitter gourd, which makes 5beta,19-epoxy-19-methoxycucurbita-6,23(e)-diene-3beta,25-diol a potential biomarker for the consumption of this food product.

   

Kuguacin A

(1R,2R,5S,10S,11S,14R,15R)-5-hydroxy-14-[(4E)-6-hydroxy-6-methylhept-4-en-2-yl]-6,6,11,15-tetramethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-1-carbaldehyde

C30H46O4 (470.3395916)


Kuguacin a is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Kuguacin a can be found in bitter gourd, which makes kuguacin a a potential biomarker for the consumption of this food product.

   

Cucurbitacin A

[(E)-6-[2,16-dihydroxy-9-(hydroxymethyl)-4,4,13,14-tetramethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate

C32H46O9 (574.3141666)


Cucurbitacin a is a member of the class of compounds known as cucurbitacins. Cucurbitacins are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. Cucurbitacin a is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cucurbitacin a can be found in cucumber, which makes cucurbitacin a a potential biomarker for the consumption of this food product.

   

Cucurbitacin K

13-hydroxy-1,6,6,11,15-pentamethyl-14-(2,5,6-trihydroxy-6-methyl-3-oxoheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-4,5,17-trione; 4,13-dihydroxy-1,6,6,11,15-pentamethyl-14-(2,5,6-trihydroxy-6-methyl-3-oxoheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-diene-5,17-dione

C60H88O16 (1064.6072048)


Cucurbitacin k is a member of the class of compounds known as cucurbitacins. Cucurbitacins are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. Cucurbitacin k can be found in bitter gourd, which makes cucurbitacin k a potential biomarker for the consumption of this food product.

   

Momordicine III

5,9-dihydroxy-6,6,11,15-tetramethyl-14-(6-methyl-5-oxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-6-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-1-carbaldehyde

C36H56O10 (648.3873276)


Momordicine iii is a member of the class of compounds known as cucurbitacins. Cucurbitacins are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. Momordicine iii is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Momordicine iii can be found in bitter gourd, which makes momordicine iii a potential biomarker for the consumption of this food product.